The Wedding Date
by bellarke
Summary: Jenny felt for her; she'd been that girl before. Waiting for the guy to notice her, or just remember she was there. Only one guy had ever really made her feel that way, but she hadn't seen him in a few years.
1. Friends and Benefits

**A/N: **There was so much potential in Nate and Jenny, don't you think? I started planning a multi chapter fic with them a while ago, but in between figuring out stories and plots I started to play around with other pairings that might come between them, and thus, this fic was born! It might be a rough ride for a while, but stay with me guys. Nobody ships Nate and Jenny harder than I do! Although I do love my angst in fanfic... Enjoy! x

* * *

**Friends and Benefits**

She'd never been more grateful that Gossip Girl was dead and gone. Or, at least, that 'she' was no longer chronicling her life. Jenny had to give credit where credit was due – she and her brother had pulled off one of the biggest schemes in UES history, and while she'd sabotaged herself one too many times, she had to admit that the likelihood of her life turning out the way it had had a lot to do with who she was in high school. If she'd never gone to Constance, she wouldn't have become the brave young woman she was. She would never have gone toe to toe with Blair Waldorf and _won_, and she never would have been able to call Blair a friend.

Sure, they'd had their issues. On occasion, they still had their issues. But the loathing between them was hidden away in a Louis Vuitton somewhere in Blair's attic and that was where it was going to stay. Now they were friends, colleagues – business partners. Successful ones at that.

'What time is it?' her… _friend_ asked from beneath the duvet. The top of his brown hair was peeping out and Jenny affectionately ran her fingers through it. It was one of her favourite things about him, of which there were many.

'Later than we'd like,' Jenny told him.

As she pulled the covers back to reveal him in his boxers, she thought about what they were exactly. They'd only reconnected a few months ago, and she used that term loosely because they were never really anything anyway. He'd spent one breakfast with her extended family years ago, and she'd seen him for the first time a couple of years before that at Serena and Blair's cotillion. That was it.

Of all the places in the world, London was where they'd met again.

_Stressed, frazzled, furious and several other things at once, Jenny had been in a hurry to get home and finish packing for her trip to Italy on behalf of Waldorf Designs. Fabrics were missing, another shipment had gone rogue and Blair was breathing down her neck to get some fresh ideas on the table by the time she came back to Manhattan. Jenny hadn't even seen the leggy blonde heading her way on the arm of an up and coming entrepreneur. Before she could side step the girl, Jenny had careered right into her and they fell to the ground in a crumpled heap. _

_Hissing in pain, Jenny examined the cut on her knee exasperatedly. There goes the mini dress for the cocktail reception tonight, she thought. Accepting the hand that was offered to her, Jenny was helped to her feet, still in one piece. Her phone, on the other hand, was in several pieces and the strap of her handbag had broken. Cursing, Jenny picked up the fragments of her iPhone and attempted to put it back together to no avail._

'_I'm sorry, we didn't see you,' the entrepreneur said with an apologetic smile as he helped his date to her feet, too. _

'_Don't worry about it,' Jenny said. 'I should have been paying attention.'_

_She chose this moment to look up and found a familiar face looking back. _

'_I know you,' they said in unison, and he smiled. _

'_Carter Baizen.' Jenny offered a small smile, given the circumstances. He'd never been very well liked among her friends and family, and though she didn't know him personally, she'd heard enough to know she should probably stay away. _

'_And you are…' he began, struggling a little. Jenny raised her eyebrows, but didn't offer any help. If he remembered her at all then surely he could dig a little deeper and pull out her name. 'Dan's sister.'_

_Jenny rolled her eyes. She'd grown up being Dan's sister, but she was so much more than just that now. Still, at least he'd tried. 'Jenny Humphrey,' she informed him, somewhat sharply._

'_My bad,' he said. He spied the J for Waldorf design on her handbag and it seemed to dawn on him that she was still a part of the Upper East Side. 'I remember Blair telling me about you during out brief – albeit fun – rendezvous.' _

_Jenny crinkled her nose in disgust for his date, and she looked quickly at the blonde. She was standing, appropriately, off to the side like a spare part, waiting. Jenny felt for her; she'd been that girl before. Waiting for the guy to notice her, or just remember she was there. Only one guy had ever really made her feel that way, but she hadn't seen him in a few years. _

_She snapped back to her conversation. _

'_I should go,' she said, sparing another glance for Carter's date. 'Let you get back to… I'm sorry, what's your name?' _

'_Tabitha,' the girl offered abruptly, stepping forward and sliding her arm through Carter's. _

_Despite this, his gaze seemed fixed on Jenny and she couldn't deny it felt a little good. Tabitha was stunning. Long legs, high heels, great bone structure, and here Carter was with his eyes on Jenny, looking her over and seeming, dare Jenny think it, __**thirsty**__. Not really one for drawing attention to herself – at least not anymore – Jenny didn't mind admitting that she liked it when guys found her appealing. She didn't look her best, really. Old, faded jeans, an even older pair of ankle boots, a plain grey vest and a black blazer fresh from the dryer. It was still creased, but she was too busy to care when she'd thrown it on. _

_And yet Carter still had his eyes on her, and they were an attractive pair of eyes too. _

_Tabitha pulled on his arm and he came back to himself, clearing his throat and hailing down a cab. Jenny began trying to fix her phone once more, setting off down the street, but just as she passed him – and with Tabitha busy getting into the cab and giving the driver directions – Carter put his hand on her arm and handed her his business card. Jenny's eyes widened in shock and she looked up at him. _

'_Seriously? You're on a date.' _

'_Just the first one,' he said, slowly pulling his hand away. He grazed the inside of her wrist and lingered there for a moment, before biting his lip and turning into the cab. 'Hope to see you around, Jenny Humphrey.' _

_With that, the cab sped off and was lost in the sea of traffic. Jenny was still staring after it moments later, his business card in hand. Shameless, she thought, crinkling her nose again. Shameless… and somehow appealing? Jenny was barely twenty four. She liked having her fun, but given her history, she'd resolved to stay away from UES men. That said, if Carter was living in London he wasn't exactly an Upper East Side guy anymore. _

That was six months ago, and now Jenny found herself staring at him, still groggy from sleep, as he stretched and ran his hands through his hair. When he caught her looking, he winked, and then stood up himself. He walked around the end of the bed and to where she was standing. He wrapped his arms around her bare waist and slid one hand down the back of her panties. Jenny's eyes fluttered and she sucked in a breath, gently pushing him away.

'I have a flight to catch,' she said quietly, struggling to get the words out as his hands roamed further and he started to kiss down her neck. One hand was on her chest now, drawing a line with his fingertip down and between her breasts.

'You could just stay,' he murmured, his hot breath now up by her ear. She reached down and grabbed his wrists to stop him.

'I have to go,' she said seriously, but she dissolved into giggles as he broke free and tickled her waist.

'Just stay one more day,' he said, pulling her back down to the bed, 'and one more night,' he went on, rolling them over so he was on top. He liked being on top.

Jenny wriggled out from underneath him and grabbed a towel from the airer. 'As fun as that would be,' she said, recalling their many, many passion fuelled nights, 'I have to get back to Manhattan. Dan's proposing to Serena and he wants me there for everything. Plus, Blair and I have to start thinking about the new line. It's getting more difficult to work from across the globe, and you know how I love staying at Casa de Bass. The sheets are divine.'

Truth be told, she'd been thinking of heading back to New York full time. She hadn't mentioned it yet, not that it would matter too much. They were just fuck buddies really, friends at a push.

'I thought you preferred my bed,' he quipped, licking his lips. At that, Jenny smirked. She went through to the bathroom and started running a bath. Carter came up and pressed his body against her back as he turned off the taps. He led her to the other side of the room.

'Don't you think a shower would be more fun?' he asked, and she couldn't disagree.

* * *

It was early evening when she landed at LaGuardia. Blair had sent a car and a change of clothes ahead for her, with a note that read:

_Impromptu benefit at the house with some potential investors. _

For as long as she could remember, Jenny had never known Blair to be impromptu about anything. Everything was meticulous, carefully planned, right down to what time the Queen B herself would make her entrance. Not one to say no to a drink with friends, though, Jenny soon talked herself into the spirit of things. She changed in the back of the car. Thankfully the windows were tinted and the driver had rolled up the screen between the front and back seats. By the time they arrived at Chuck and Blair's house, the evening seemed to be in full swing. Jenny's suitcases were taken upstairs by Dorota, who Jenny greeted with a kiss on the cheek.

'How are Leo and Anna?' she'd asked, and Dorota had beamed with pride.

'Very good Miss Jenny, thank you. Miss Blair is wanting to speak with you.'

Jenny waved her off and walked ahead through the house. Strangely enough, it had become something of a sanctuary for her over the past few years. She felt safe there, like she was truly home. She was stopped in the living room by Dan, who swept her up in a bear hug, and then by Serena who drew her in to an even tighter hug and kissed her on both cheeks.

'Jenny!' her future sister-in-law – and former step-sister – flashed her famous smile. 'How are you? How was your flight?'

'Good and good,' Jenny said, accepting the champagne Dan had retrieved for her. 'Thanks. Have you seen Blair?'

Serena was still grinning, though Dan was noticeably less enthused all of a sudden. Jenny looked between them and waited for an explanation, but it didn't come. Instead she was surprised to find Chuck had snuck up behind them. He touched her back and she turned to embrace him.

'Jennifer, I trust your journey was pleasant? You look stunning.'

He was the first to comment on the dress Blair had sent over. He must have known it was his wife's choice. The dress was long, black and flowing but the ends of the fabric dissolved into lace by the time it hit the floor. It had some thick straps that criss-crossed over her back, and a cleavage enhancing v-neckline.

'Thanks Chuck. Is Blair around? Apparently I'm in demand.'

'Yes you are.'

Jenny turned once again, worried she might have a spell of dizziness. She found Blair crossing the room, and soon was engulfed in yet another tight hug. Blair then took her by the arm and led her through to Chuck's study, where she closed the door on the party so that it was just the two of them.

'What's going on, Blair?' Jenny asked, crossing her arms. She knew the woman pretty well, and she recognized the glint in Blair's eyes. There was a scheme at hand.

'You'll be happy to know that I've acquired you a date for the wedding,' she said, looking pleased with herself.

'What?' Jenny blurted out. 'Dan hasn't even proposed yet!'

Had she missed it? Why wouldn't Dan have said something? And why did Serena look so happy if they weren't even engaged yet?'

'Relax, Little J. As far as they're concerned it's just a potential suitor, but I happen to have a good feeling about this one. I fully expect him to be your date to the upcoming Humphrey-Van der Woodsen nuptials.'

'So he hasn't proposed yet?'

'No. Keep up, Jenny,' Blair admonished.

'Right,' Jenny said, grip tightening on her clutch bag. Her – now in working order – phone was inside, as were the many phone logs and text messages she'd exchanged with Carter. Suddenly she felt guilty about her somewhat double-life, and most of all about him. But they weren't serious. On cue, her phone sounded in her bag to alert her to a new message.

'Aren't you going to get that?' Blair asked, circling Chuck's desk and smiling fondly at a picture of their son, Henry.

'No,' Jenny said, in what she thought was a convincing tone. Blair stopped and eyed her suspiciously.

As much as Jenny liked to think of herself as a strong young woman, and a gifted liar, something about Blair always left her feeling not quite up to par. She couldn't lie to Blair, and sadly this was the one time she really should have been able to. Blair narrowed her eyes and moved towards her.

In an effort to distract her as her phone sounded for the second time, and then a third, Jenny tried a little too emphatically to change the subject.

'So who's the guy?'

The door to the study opened just then.

'Blair? Chuck said you were looking for me.'

Jenny's breath hitched as Nate walked right back into her life. It had been years, and he still looked as impossibly handsome as ever. Whenever she was in the city she just so happened to miss him by a few hours; she was always dashing off to London or Italy or Paris whenever he'd stop by, and he was busy over in Los Angeles.

In the time Jenny spent staring at him, Blair had snatched the clutch bag from Jenny's unsuspecting hands and pulled out her phone.

'Nate,' Jenny breathed.

'Jenny,' he replied, a gorgeous grin spreading across his face. Jenny smiled, but the moment was short lived, as Blair's shrill, scolding tone rang out in disgust.

'Carter Baizen!'

* * *

**A/N: **Wasssssuuuup? Hope you liked that little intro there. I totally get it if you're maybe a little confused over the time frame and where Jenny actually lives. She's sort of between places and has been for a while because she travels so much as part of her job. Carter became a sort of security blanket in London, where as Casa de Bass became that for her in New York. I always imagined Jenny as being someone who couldn't settle in one place or another for too long because she never really knew who she was. Is that a bit too philosophical? Whatever.

As for the timeline, I imagine Jenny arrives back in NY for Dan's proposal, roughly around four months before he and Serena tie the knot. I don't imagine it was a long engagement at all!

Thanks for reading this chapter, and I hope you stick with the story for the rest. Much more to come!

Please leave some feedback? It's better than cake, and it helps me get better! x


	2. Wanton Humphrey

**A/N:** Howdy guys. Thanks for coming back. This story has officially been bumped to an **M** rating, and you'll see why when you get a little insight into Jenny and Carter's past. Read at your discretion ;)

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**Wanton Humphrey**

Since giving birth to her son, Blair's maternal instincts had become just that._ Instinctive_, as is the norm in new mothers. Not that this was new. She'd long considered herself the mother hen to her less intelligent, and by far sillier, friends. As such, she often found herself scolding her friends and family when they made bad decisions. Since this was, regrettably, a regular occurrence, Blair could often be found lecturing an unwilling participant in Chuck's office. It didn't matter if he had work to get on with at home – the room was usually engaged. It was really the main reason Chuck was overseeing plans to renovate one of their first floor reception rooms into an office for Blair. She had her atelier in the city and, given that she shared it with Jenny on occasion, it would have made sense for Blair to lecture Jenny there.

Given the urgency of the situation, though, Blair knew she needed to nip this travesty in its bud sooner rather than later. So she found herself, in the middle of a benefit for the local hospital, pacing her husband's office while Jenny Humphrey sat in one of the chairs facing Chuck's desk. Nate was standing awkwardly just inside the door, which Blair had insisted he'd closed behind him.

She was holding Jenny's cell phone gingerly in one hand, the other placed firmly on her hip as she walked.

'Jenny' she began. 'I understand, likely better than most, that Carter Baizen comes with a certain appeal. He's a bad boy; corrupted, and corrupting. But he'll always be a bad boy, and bad boys are not fit for queens of Constance.'

Jenny tried to interrupt, but knew it was fruitless. She cast a look at Nate, but he immediately ducked his head. Blair sat down opposite Jenny and clicked her fingers, drawing the blonde's attention right back to her.

'Let me set the scene, if I may. It's 2007. Carter returns to the city after a prolonged absence, broke and supposedly a good man. He invites our dear friend Nate to a poker game, only to set the young Archibald up to take the fall for his own debts. Luckily my husband arrives in time to stop any serious damage being done. Moving on, it's 2008. I am at a vulnerable point in my life, and Carter Baizen seeks to exploit that in order to gain a one up in his ongoing war with Chuck. He and Serena, thankfully, see to it that he leaves the country.'

'Let's fast forward again to 2009. Serena has been searching for her father with help from, of course, Carter Baizen. Once again his debt catches up to him, and he leaves her in the lurch after she and Nate jeopardized their friendship in order to help him. He returns in 2010, when Nate and Serena are finally acting on their feelings, and reveals he's found her father, but he withheld the information for a while in order to try and win her back.'

Jenny stared at her, mouth slightly agape across the desk. Blair didn't flinch; she knew she was impressive.

'What I'm getting at, Little J, is that Carter is no good. He's no more fit to be your boyfriend-'

'Carter Baizen is your boyfriend?'

Nate finally spoke up and Blair and Jenny turned their gazes on him. His arms had fallen to his sides in surprise, and while his demeanour was mainly that of shock, his eyes were dark and somewhat worrying in the way they were looking at Jenny. He was jumping to conclusions, and with that he was judging her. Silently, and to herself, Blair smirked. For years she'd wondered at the compatibility of her two friends.

Despite her previous wars with Jenny, and the fact that the timing was never right, Jenny Humphrey was more than a match for Nate Archibald. And now, with Dan proposing to Serena and the likelihood of a wedding being a guaranteed one hundred percent, Blair pondered that maybe it was time for Little J to get her moment in the sun. God only knew Jenny had been mad about the boy since she was fourteen, and there was plenty of unresolved tension there.

'He's not my boyfriend,' Jenny said earnestly, though she'd turned from Nate in favour of convincing Blair.

Blair raised her eyebrows and set about finding the text messages Jenny had received earlier. Upon unlocking the phone, she reminded Jenny that she really ought to have password protected it.

'Blair come on,' Jenny protested, rising from her seat. 'That's private!'

All trace of games and arrogance drained from Blair's face. She paused for a moment, then handed Jenny the phone. 'I'm doing this for your own good, Jenny. Carter is bad news, and you should keep away.'

'People change,' Jenny argued, stuffing her phone back into her clutch and zipping it closed with force. 'You should know that better than anybody, just look at Chuck.'

'Carter Baizen is no Chuck Bass.'

It was Nate who spoke. Blair didn't argue, of course, but Jenny wasn't finished.

'I changed too,' said the Brooklyn native. 'Just look at who I was six years ago – at all the things I did.' She stopped herself, looking quite ashamed, and turned her gaze on the ground.

Blair felt a kick in her chest, but nothing more. She and Jenny had long buried the hatchet and though the memories of that night were something Blair liked to keep hidden away, never to be disturbed, she could admit now that she understood. Jenny was her friend. She'd forgiven Serena and Nate for the same thing, though with Chuck the pain has been so much worse. Every part of her had ached, but it was in the past. She and Chuck were storybook, meant-to-be epic, and nothing could come between them.

'Look, I don't have to defend myself about this,' Jenny said, folding her arms. 'I'm nearly twenty four. I make my own decisions and I can look out for myself, okay? I appreciate the concern, but like I said, Carter is not my boyfriend.'

'Then why's he texting you?' Nate asked, his tone unfaltering.

Jenny shrugged. 'We're… we're friends. We met in London about six months ago and we've been hanging out-'

'I knew those business trips were suspect!' Blair interjected, pointing an accusatory finger Jenny's way.

'You've been sneaking off to London to see him,' Nate said, struggling to grasp the idea. He seemed to be taking issue with it. 'But you're just friends?'

'I haven't been sneaking anywhere. Look,' Jenny said, throwing up her arms and making for the door. 'I'm tired, and I don't have to explain myself to you. I appreciate the concern, but Carter is different now, and we're _just_ friends. Now, if you'll excuse me, I'm going to go and sleep this off. Blair, I'll see you for breakfast at seven. Nate…'

She stopped next to him at the door.

'It was nice to see you.'

Blair watched her go, and Nate soon followed, citing that he needed a drink. Her plan had been disrupted, but any good Queen B has plans B, C and D ready to go. Of course, now that Carter was no doubt in the mix, things were going to get complicated. But Blair was more than able to coax people over to her way of thinking, and with Carter all the way over in England and Nate right on Jenny's doorstep, it wasn't going to take much convincing until Jenny saw things her way. The right way. Surely.

* * *

Nate was feeling particularly tender the following morning. After his first drink of the evening, which had followed the unearthing of Jenny's friendship with Carter Baizen, he'd had another, and another, and another and soon he was being persuaded to stay in the Bass' second guest bedroom. Jenny was in the first, he remembered as he tiredly got dressed before heading down to breakfast. He had a free morning, which came as a welcome relief from his endless days and nights working on the Spectator's latest expansion.

He was overseeing the opening of their new office in Los Angeles. He'd been spending weeks – sometimes months – at a time over there. He'd been back all of one day when Blair's name flashed up on his cell and she'd insisted that he come along to the impromptu benefit. Nate had never known Blair to be impromptu. He suspected foul play, but had no idea what her game was. Since Henry's birth both she and Chuck had cooled it with the schemes, though they still crept up every now and then.

As he descended the stairs, the hustle and bustle of the Bass household found him and he smiled when he heard his godson's laugh coming from the dining room. He found Blair and Chuck in there already with Henry, and they all bid him a good morning. He ruffled Henry's hair as he passed the little guy, then turned his attention to Jenny, who was sitting opposite the three of them at the table. Nate took the empty seat beside her, where a place had been set for him already, and smiled in greeting.

'You look how I feel,' Jenny said, reaching for a plate of fruit.

'You're hungover, too?'

'Nope, jet lagged. Between Paris and Italy and London, I'm exhausted.'

Nate's stomach clenched at that. _And London_. _And Carter Baizen_, he thought. He'd always known Jenny to pursue the wrong kind of guys, from Asher to Damien and now Carter, but surely even she knew that Baizen was just one creep too far.

He regarded Jenny for a moment. She was certainly grown up, a far cry from her final days at Constance. Gone were the ragged extensions and black eyes, replaced by well kept, flowing blonde locks and, at that time in the morning, no make-up. She looked every bit the picture of perfection, and their brief, but sweet, time together his senior year of St. Jude's had opened a door between them that had never really been closed.

Despite everything she did before she left, including trying to sabotage his relationship with Serena and sleeping with Chuck, Nate had never turned his back on her. Not completely. They were friends; he'd trusted her with secrets about Serena, about his parents, his whole life, and that didn't go away just because Jenny lost herself for a little while.

She'd come back in the end.

'Nathaniel?'

'What?'

Nate tore his gaze from Jenny when Chuck spoke, only then realizing he'd been staring at her. He cleared his throat and accepted the Wall Street Journal from Chuck, though he wasn't much in the mood for reading. Ignoring the smug look on Blair's face, he set about reading the first page. He was beginning to think he needed glasses though; all those long hours staring at computer screens and reading and re-reading drafts of stories were starting to take their toll.

'As I was saying,' Blair said to Jenny. 'There's still the issue of the fabrics over in London, but I can handle that this week. You could take a look at the designs that have come in from Italy for me. I trust your eye to choose the best ones for the line.'

'No problem,' Jenny said, but her tone suggested she wasn't quite happy about it. 'But I can _handle_ London. You haven't met with the team there in ages – it makes sense for me to just carry on as I have been.'

'No, I insist,' said Blair in a sickly sweet tone.

Jenny rolled her eyes, but didn't seem annoyed. More exasperated than anything, Nate decided, as she puffed out the air from her cheeks. She excused herself to go and get dressed, and after a few moments, Nate slipped out under the pretence of going to the bathroom. He caught up to her as she was halfway up the stairs, and by the time he'd called after her they were on the first floor landing, heading to her room.

'It's great to see you,' he said.

'You too,' she replied with ease, tightening the tie of the robe she had on.

They walked on in silence, but the weight of the words they weren't saying seemed too much to bear, and Nate gave in.

'I'm sorry I was so out of touch these past few years,' he began, just as Jenny spoke too.

'Sorry I haven't kept in touch so much.'

They chuckled at one another as they came to Jenny's door, but Nate wasn't quite satisfied with leaving it there. He'd always found her interesting. In fact, she always left him curious, and now with all of this coming out about her and Carter, when she seemed to be doing so well for herself – away from all the drama the Upper East Side entailed, Nate felt it was only right that he try and get through to her where Blair had failed the night before.

'Listen, Jenny, about Carter…'

'Just friends,' she reminded him.

'If you say so, but please just listen for a second.' She didn't say anything, and so he took it as a sign to carry on. 'He always came across the good guy at first, but in the end he just couldn't stick it out. Deep down, he's no good.'

'People change,' Jenny repeated.

'Some people do, yeah. But he's not one of those people.'

'How do you know that?' she challenged, placing a hand on the door to her room. Nate was sure she was about to disappear on him, and a feeling in his gut suddenly had him scrambling to find ways to make her stay.

'I just do. I know plenty of guys like him.'

'I really don't want to have this conversation again,' Jenny said, opening her door ajar.

'Alright, fine,' Nate said, a little too eagerly. He took a breath. 'Look, what I really came to say was that I think it'd be good for us to hang out some time, for old times' sake? I feel like I barely know you now.'

Not true of course. He'd always know Jenny Humphrey, likely better than she knew herself.

She didn't seem as convinced as him, he realized, as she bit her lip. 'I don't know, Nate. Things between us have gotten complicated in the past… I don't want to drag that all up again.'

'Hey,' he grinned. 'People change.'

She smirked and stepped into her room. At length, she agreed. 'The diner we went to for your birthday?'

Nate knew the one. He'd been treated to a real Humphrey birthday, complete with public humiliation.

'Sounds great. I'm in meetings all afternoon but how about tomorrow for lunch? One thirty?'

She gave him a great big smile and nodded, before closing the door.

It could have been the fact that he was just now properly waking up, or it could have been the smell of coffee and bacon as he went back to his breakfast. He was feeling clear-headed, and his hangover seemed to be lifting quickly. It might have had more to do with Jenny Humphrey making him feel seventeen again in amongst the stress of being a twenty six year-old Editor in Chief, but that was neither here nor there. He wasn't so sure what it was about her that brought it all out in him, but he liked the feeling.

* * *

When she was safely tucked away in the window nook later on, overlooking the streets of Park Avenue from her guest room at the Bass', Jenny flipped open her Macbook and began scanning her emails. Italy, Paris, even Madrid was calling and, further down the list, London. She smiled.

She'd never expected this level of success at such a young age, but she always knew she'd be successful one day. Blair had mentioned a promotion in the coming months, one that would see Jenny needing to permanently settle in Manhattan, leaving behind the glorious life of a well-travelled designer and instead find her heading up her very own design team at Waldorf Designs, answering only to Blair herself. She'd be second in command.

It would be a huge honour, and while Jenny was on board with moving home full time, something in the back of her mind nagged her about leaving the travelling behind.

As if on cue, Jenny's phone rang. When she spied who was calling, she glanced quickly to the door to be sure it was shut tight. One never knew in the Bass household, and the walls probably did have ears. She slid the answer button across and pressed her phone to her ear.

'Good morning.'

'Good afternoon, beautiful,' Carter countered on the other end.

It would be going on one in the afternoon there, Jenny figured. She relaxed back against the wall and settled her gaze on a group of high school students making their way to school.

'What can I do for you Baizen?'

'Always so direct,' he mused, and Jenny could just tell he was lounging in his chair in his office, feet up on the desk, smirking at every word she said. 'You never answered my texts last night.'

Memories of the previous night's fiasco appeared at the forefront of her mind, and she sighed outwardly, loud enough for him to realize something was wrong.

'What happened? Are you okay?' the alarm in his voice was unfamiliar, but not unwelcome. In fact, Jenny found herself wishing he would just catch a flight out to New York so they could show her friends that nothing was going on.

Alright, something was going on, but it was purely physical, and Jenny liked it that way. Since her disastrous exit from the Upper East Side all those years ago, Jenny had struggled to connect with people. Not just girls, but boys. With the girls, she could never tell which ones wanted to be her friend purely because they liked her, and which ones were hoping to gain some insight into the 'scandalous lives of Manhattan's elite', as Dan had so elegantly put it when he'd dreamed up the idea of Gossip Girl so long ago. With the boys, she never knew which ones to trust. It dawned on Jenny, somewhere in between arriving in Hudson and finishing her first week at school there, that the only boy she'd ever really trusted – outside of her family, which included Eric – was Nate.

And she'd royally screwed that up.

But now she had Carter; a genuine friend who understood her. He understood what her life in the UES had made her, how she'd lost herself in bitter hatred and struggled to cope with it all until she ran away. It just so happened that this new friend she'd made was someone the rest of the people in her life, simply put, _detested_.

'Jenny?'

'Sorry, I'm tired. I'm still on London time.'

'What's going on?'

'Nothing, I'm fine.'

'Liar,' he said, and he was right, but they didn't dwell on it. 'I was just wondering if you'd planned your next business trip yet.'

'Is your bed that cold already?' Jenny could practically hear the grin on his face through the phone, but it wasn't one she returned. In fact, her stomach took a turn and she felt guilty. Biting her lip, she clicked open an email from Blair and found a jam-packed schedule for the next few months. All the events were in New York.

'About that,' Jenny said at length, and then closed her laptop. 'Looks like I might not be back for a while. If at all.'

He didn't answer right away, but the silence was deafening.

'Carter?'

'Not a problem,' he said suavely, but Jenny knew him well enough by now.

Carter made no secret of the fact that he liked sex. In particular, he liked sex with her. Of course he was going to be a little disappointed. The friendship part of things would be fine; they could email and text and call. But the sexual part… well, Carter was going to have search long and hard for someone who could so intricately get to know his body like she did. Likewise, Jenny knew she'd have a hard time finding anyone to quench the thirst that Carter left her with every time they finished. He satisfied her in every way, but it was never enough. She always wanted more of him. Her mind began to drift, and soon enough she was reliving their first… encounter.

'_Before…this…gets… out of-oh!' _

_Jenny knew her attempts at conversation were futile. With every word, Carter seemed to find a new place to make her feel incredible, and she was starting to lose her grip on reality. He had her up against the wall of her apartment, legs wide apart as he worked his way further and further down. Her underwear was pushed to the side as his fingers scraped the inside of her thighs and it was all she could do to keep herself from digging her nails into his shoulders. She grabbed his head and pushed him down, fingers rushing through his hair. _

_He was on his feet suddenly, one hand tangling in her hair and the other grazing her jaw, denying her the release he'd had her craving. He looked her dead in the eye, and all she could think was that she wasn't done with him yet. She kissed him hard, all tongue and hot breath and teeth scraping as her hands went to his belt and ripped it away from his trousers. His shirt came off next and was discarded in the living room. She guided him through to the bedroom, and he lifted her around his waist to carry her to the bed. _

_He threw her down and attacked her with kisses again. On the mouth, along her jaw, her neck, her collarbone. He ripped open her shirt, the buttons springing in all directions, and kissed her breasts along the top of her bra, but didn't wait long to pull it down. His hands went back up to her wrists, pinning them above her head. All she could do was writhe under the pleasure. _

'_What was it you were going to say?' he murmured, trailing teasing kisses along the hem of her lingerie._

_Jenny pulled him back up, so that they were pressed up against each other with him on top. She tilted his chin up with one finger as the other hand roamed his chest. _

'_This is just a one-time thing,' she replied, and he smirked. _

'_Whatever you say, Jenny Humphrey.'_

Carter's distant voice broke in. 'Jenny, you still there?'

Coming back to herself, Jenny had to force herself to speak. Her mouth was a little dry.

'My birthday is soon, don't forget.'

'Of course. I'll send something.' And by that, Jenny knew that he meant his assistant would send something. Erin had always had much better taste than him anyway. 'I should go,' he said.

'Alright. Talk soon?'

'Sure thing. Bye.'

'Bye.'

As the line went dead, Jenny couldn't help but feel a little disappointed. She thought back to her schedule, ready to get on with her day. Before anything else, though, she needed a shower.

* * *

**A/N:** Hope you liked this one - more to come, and the drama hasn't even started yet!

Please leave some feedback - it's heavily appreciated! xoxo


	3. Sage Advice

**A/N:** Regrettably, there are some discrepancies in the time frame in which this story takes place. Currently, Jenny is 23, and the Gossip Girl Wiki (I'm a thorough fact checker, me!) states her birthday as being on April 2nd. Based on the ending of season 6, I always assumed that Dan and Serena married around September time, because I felt we were being introduced to a new wave of Constance kids as they headed off to school to start the year.

Being that this story takes places roughly four months before the nuptials, and with Jenny still 23, I've decided that her birthday is now in June. It isn't crucial to the plot and therefore really doesn't matter, but I just wanted to get that in there to put to rest any confusion. If there even was any. If you didn't notice, or simply don't care, then let's just leave it there.

Moving on!

In this chapter, we delve a little bit further into Jenny's past, and touch very briefly on how she and Blair came together to create J for Waldorf. Despite their growing friendship being the primary one in Jenny's life as she readjusted, I always felt that in order to come back to the Upper East Side, Jenny had a lot of bridges to mend. Not least of all with Serena, which is what the flashback centres on. Let's be honest, Jenny made things preeetty difficult for our favourite golden girl in seasons 3 and 4. She owed S an apology.

But that's enough from me for now. Enjoy!

* * *

**Sage Advice**

'B, we really should just stay out of it.'

'Nonsense. The very well-being of our friend is at stake here.'

'I think that's being a little dramatic.'

Serena had more important things to worry about that day, and while she cared about Jenny just as much Blair - if not more – she knew that Jenny was perfectly capable of taking care of herself. And honestly she just didn't believe Jenny would be silly enough to date Carter Baizen. The stories about him from strangers were enough to turn anyone away, let alone stories from close friends and family. She'd grown to think of Jenny as a sister. They'd been sisters before, obviously, but not by choice. Now that Serena planned to spend her life with Dan, Jenny came as part of the package.

It was a package that Serena loved and trusted dearly.

Still, the persuasive tones of her best friend were difficult to resist. Blair Waldorf Bass was a well-oiled, perfectly manicured little machine. Serena huffed into the mouthpiece of her cell, tapping her foot.

'I'm actually meeting Jenny in a couple of minutes.'

'Wonderful,' Blair cooed on the other end. 'Now, I need details. How long, how often –'

'How often?!' Serena screeched, outraged.

She caught the eye of a middle-aged man sitting a few tables over and offered a smile in an attempt to recover some of her dignity. He promptly cleared his throat and fluffed out his paper, as if he hadn't even noticed her there.

'Really, S? You're going to play coy? We need to get to the bottom of this thing between Jenny and Carter, and snuff out the torch before his ship makes port again.'

'Oh my God,' Serena groaned, covering her face with her hand and leaning her elbow on the table. 'Blair, that's enough. She said they're just friends.' The door chimed and Serena looked up. Jenny waved and began making her way over. 'She's here, I have to go.'

'Find out!'

'Alright mom, I love you. Bye! Jenny, hey.'

Serena stood up and kissed her on both cheeks. She caught a breeze from the door as it swung shut and was thankful for it. It was turning out to be one of the hottest days of the year so far, and being only June, Serena was excited for what the summer would bring. Partly, anyway. She was also terrified of making it to the end of the month for a couple of reasons. The first was Dan. He was acting strangely, and had been for weeks now. He seemed nervous around her and dodged questions like where they would spend Christmas, and what Jenny might like for her birthday. It was almost as if he wasn't planning on being around. Serena knew she was probably, most likely, almost definitely over thinking things, but it wouldn't help to get a second opinion. That was where Jenny came in.

Few people knew Dan Humphrey as well as Serena did. Jenny was one of them.

The second reason she was dreading and wilfully expecting the end of the month in equal measure was this:

Serena was late.

'How's Lily?' Jenny asked, sitting down. She picked up two menus and handed one to Serena.

'My mom… is great, thanks. She and Dad are enjoying Bali at the moment.'

'I'm surprised they get cell reception over there. Weren't they staying off the grid?'

Serena smiled and bit her bottom lip. 'Right. Yeah. Lucky five minutes I guess.'

Jenny was looking at her suspiciously. Serena's ability to bend the truth used to be pretty good, given who she was best friends with, but Jenny had been fierce in that respect too, and being queen of Constance had taught her a few things. Serena knew right away that Jenny could see straight through her, but she soldiered on so as not to disappoint Queen B.

'How are things? Are you excited for your birthday?'

Jenny smiled broadly. 'I am. Things are going well right now. I'm finally inspired for the new line – Blair and I bounced some ideas around this morning and we're even thinking of dabbling in menswear. High end couture suits, that kind of thing. She also mentioned a promotion which is really exciting. I think I'd like to be back in Manhattan,' Jenny paused briefly. 'As long as I could keep my feet on the ground and my seventeen year-old self at bay…'

Serena was nodding along as Jenny spoke, taking in her words but not really listening. She was bursting with questions and panic and worry and just couldn't hold it in any more.

'Is Dan going to break up with me?' she wailed, staring at Jenny across the top of their menus.

Jenny's eyebrows went up in surprise, and Serena couldn't blame her.

'Are you kidding?' Jenny asked, completely serious, as she set down her menu. 'Serena, no of course not! Why would you even think that?'

'He's been distant lately, acting weird. Every time I bring up anything to do with the future, from your birthday to this Christmas and next year, he gets all wordy and nervous and finds a way to change the subject, or drops the conversation.'

Serena could hear herself getting clingy, but she just didn't care. When it came to Dan Humphrey, she was as clingy as she cared to be, and as loving and loyal and lovely as she could be. Jenny's expression had changed from surprise to something else. She was trying not to look Serena in the eye. The guy with the paper a few tables away was _not_ that interesting.

'Spill,' Serena said, eyes narrowing.

'There's nothing to spill,' Jenny insisted, slapping on one of her most eager smiles to date. She grabbed at her menu again. 'I might get eggs. Do you want eggs?'

'Jenny.'

'But then I am a Humphrey, and the waffles here are so good.'

'_Jenny_.'

'Dad would flip if he thought I was eating anyone's waffles but his own-'

'Jenny!' Serena had hissed and stolen the menu away. 'Tell me.'

Jenny was resolute and refusing to budge, so Serena had to invest in her Blair tactics. She pursed her lips and leaned in, quirking one eyebrow just enough to make Jenny sweat under her gaze.

'Fine. If we won't talk about Dan, let's talk about Carter Baizen.'

Jenny's otherwise engaged gaze froze on Serena and she visibly stiffened, before dissolving into a guilty little sister.

'I can't tell you what he's planning!'

'He's planning something?'

Jenny realized her mistake. 'No…'

'What's he planning?'

'Nothing!'

Serena grinned and sat back, triumphant. 'He is planning something. Is it a weekend getaway? A vacation in Europe?'

'I'm not saying anything else.'

Serena clapped to herself, still smiling, and then reached for Jenny's hand across the table. She'd been so worried this morning and now her mind was half at rest. With the issue of Dan out of the way, she could focus her energies more on the issue of her late period. It was probably just the stress of worrying about her relationship, and she'd get it soon enough. She felt Jenny squeeze her hand, and saw the look in the youngest Humphrey's eyes. She'd seen it before, a few times. Once at Serena's mother and Rufus' wedding, when they'd said their vows, at the guerrilla fashion show when she'd seen how much people loved her designs and she'd run into Nate's arms, and then again when she'd returned to Manhattan in the Spring of 2015, two years earlier.

Jenny looked so happy, Serena mused, as butterflies flew in her own stomach. Good things were coming, she could tell. She'd forgotten entirely about the Carter Baizen situation.

* * *

'_Just take my advice,' Blair chided her. _

_Jenny rolled her eyes on the other end of the phone and somehow, she thought, Blair probably knew and it only added to her irritated tone. _

'_I don't know if this is a good idea.'_

'_Of course it is,' Blair said sharply. 'Jenny, we've been through this. Waldorf Designs would like to bring you aboard, but we won't be welcoming you back to Manhattan while there are so many unresolved issues between you and my circle.'_

'_Right,' Jenny conceded. 'Okay. I'll call you when I land in Paris. Can you email the itinerary, please?'_

'_Already sent, mon ami. Now get to it. Au revoir!'_

_Blair clicked off just as Henry began sobbing in the background. Jenny heard enough to know Henry wanted his Daddy. _

_Considering Serena Van der Woodsen was one of the nicest people on the Upper East Side, at least that Jenny had met, she'd never been so nervous to talk to her. As she rode the elevator up to Serena and Dan's apartment in her old building, Jenny wondered which of Serena's famed personas would meet her when she arrived. It could be her loveliest one, wherein she loved everything and everyone, or it could have been the brief, head-bitch-in-charge one she'd adopted briefly at Constance during her war with Blair. Jenny hoped it was the former, and given Serena's unearthly capacity for forgiveness, she didn't think it was too much of a stretch to hope for it. _

_They'd seen each other in the few years since Jenny had left Manhattan for good, at Christmases and birthdays, but they'd never spoken a great deal and, honestly, Jenny didn't blame her. It wasn't just that she'd sabotaged Serena's relationship with Nate; that was child's play and in the past, and Serena was in love with Dan. The real, lingering issue between them was what had happened during Juliet's run of terror. _

_She'd convinced Jenny to help in her plan to take down Serena, and it had escalated so quickly that Jenny became caught up in consequences she hadn't intended on. Jenny had gone straight to Blair to set things right, which she knew did little in terms of gaining Blair's forgiveness for the Chuck incident. But it had set Jenny on the path of redemption she'd so clearly needed. _

_She was at their door before she'd had a chance to look up and, knocking thrice, she stepped back and waited. Dan was at a signing, which oddly Jenny preferred. It would be better for her and Serena to do this alone. The door opened then, and as the sunlight hit her hair, Serena stepped forward in a mane of gold. Glorious as ever, Jenny thought. Unlike her teen years, there wasn't a hint of resentment in her mind. Serena smiled. It was small, but it was there. _

'_Hi Jenny.'_

'_Hi.'_

_They spoke at length, for what seemed like hours, and drank tea and ate some cake Serena had made. She claimed she was nesting, and Jenny had laughed. Being in Serena's company had never been this easy before, not even in Jenny's freshman year at school. Back then Serena was terrifying, in a good way, and it took a while for Jenny to grow into herself. When she did things went a little downhill, but that was neither here nor there. Serena asked about her designs, and she asked about Serena' charity work. She was the head of several committees at just twenty five years old – a far cry from her cotillion introduction. Serena was still consulting on films here and there, and she'd become a great reader of Dan's work, offering notes and suggestions. _

_Jenny envied the way Serena and her brother just seemed to fit. Anything else didn't work. That was something her teenage self would agree with, but for all the wrong reasons. _

'_Serena,' Jenny said a little later, when they'd settled into the more serious side of things. 'I'm so sorry. For everything with Juliet. I never wanted any of that to happen. I was an angry, selfish kid.'_

'_I know you're the one who told Blair what happened,' Serena said, setting her tea aside. _

'_Doesn't make up for it,' Jenny said, dismissing Serena's understanding. She didn't deserve it. 'And I'm sorry about Nate. Trying to sabotage the two of you. I was so stupid.'_

'_You loved him,' Serena said, like it was fact. Jenny couldn't argue. _

'_I think I loved the idea of him back then-'_

'_No.' Serena reached over and squeezed her hand. 'You did. First loves never really go away, either. They mark you. They keep in your memory and your heart.'_

'_Doesn't matter anyway,' Jenny said, half-laughing at herself. 'Nate never saw me as a viable option.'_

'_Given the way he looked at you after your fashion show at my Mom's event, I don't think that's true.'_

_There was a pause as Jenny thought back to that night. If she could go back and relive any one day of her life over and over, it would be that one. She'd finally shown people what she could do, what talent she had. Agnes wasn't a crazy bitch yet – she was a genuine friend, and Nate… Nate wanted her. She could feel it in the way he'd kissed her. That was something she did relive sometimes. _

'_Jenny, do you still care about him?' _

_Jenny shrugged. She could feel tears pricking on her lash line but blinked them away. 'I think I always will, but that's all in the past and it's better left there I think.'_

_Serena leaned over and drew Jenny into her. 'If you'd seen the kind of things I got up to not that long ago over Dan and Blair, you wouldn't feel the need to apologize. But thank you.'_

_They let go and Jenny held up a plate of chocolate cake. 'All is forgiven?'_

_Serena giggled her famous giggle. 'All is forgiven.' _

_They ate and drank more until Jenny had to head to the airport to catch her flight to Paris. On her way out the door, Serena gave her another hug. _

'_You know, Jenny, just because you think something's better left in the past, doesn't mean it is. Look at Dan and me. He fell in love with Blair, but ultimately he and I were meant to be. I think sometimes people need to be apart, so they can realize they need to be together.'_

_She squeezed Jenny's hand and said a final goodbye. On her way to the airport, Jenny couldn't help but feel calm. She was repairing her relationships and everything she'd damaged in her wake when she'd declared war on the Upper East Side, and it felt good. Having Serena back in her life was surely going to be a blessing, and working with Blair was making her happier than she'd been in a long time. Things were looking up. _

_There were others she'd inevitably have to face, but they were for another day. For now, she was going to enjoy Paris and, perhaps, wonder at Serena's words._

* * *

Nate was feeling hounded. In between meetings, he'd managed to steal away a break in his office at the Spectator. Head in his hands, he sighed heavily and closed his eyes. There was a lot of talk surrounding him lately. Not about whom he was dating, if he was dating, if he was even straight or anything else to do with his – currently failing – love life. It was all to do with a tip that had been leaked to the Post. Apparently Nate was planning on running for mayor. This was all news to him, of course. His grandfather had made the call to him some days earlier, overjoyed at the news and demanding to know why he hadn't been included on the matter.

Nate had been quick to dash his hopes, but still the journalists called for quotes and asked for interviews. His assistant, Katie, just so happened to be going away on maternity leave too, and that only added extra strain. She was superb at handling these kinds of things. He was going to miss her. But she had more important things to attend to, obviously. Speaking of, he still had to get through the pile of applications to cover the position while Katie was away, and he hadn't even looked at them yet.

Just as he turned his attention to them, he heard Katie talking with someone in the hallway.

'Do you have an appointment?' Katie asked.

'No, but don't worry. We're old friends!'

He checked his watch. Was he late to meet Jenny? Had she tracked him down? His stomach gave an involuntary leap at the thought. He stood up and straightened his tie, and just as the door started to open he cracked a grin. But it wasn't Jenny who met him at the threshold. Instead of leaping again, his stomach plummeted.

Sage Spence was, most certainly, not Jenny Humphrey.

'I'm sorry, Nate,' said Katie, glaring daggers at the back of Sage's head. 'She just barged right past me. I can't exactly fight her off.'

Nate shook his head. 'It's no problem, Katie. Why don't you take a break? Put your feet up.'

She looked grateful. 'Thanks, Nate.'

He closed the door on her as she walked away and then turned back to Sage. She was sitting on his desk; impossibly tanned legs crossed in front of him, on full display thanks to her – inappropriately short – black skirt. She was biting her lip and smirking as he came closer, but Nate wasn't exactly in the same frame of mind.

'You can't just barge into my office, Sage,' he said with authority, though his hands in his pockets gave off a distinctly casual vibe. She didn't seem to mind either way though. She turned to her satchel and pulled out a thin file.

'My résumé,' she said, handing it over. 'For the assistant position.'

Nate eyed her, eyes slightly creased, and tried to figure out if she was making fun of him. The last time they'd seen each other had not been very pleasant. It was his twenty third birthday, and they'd really been on the rocks for a while. She was busy choosing colleges and wanted to stay local so they could go on as they were, but Nate felt the relationship was coming to a natural end and, honestly, he was looking for something more mature. It surprised even him, and when he brought up the fact that there was a significant age difference, she went on and on about how it hadn't seemed to bother him when they were in bed together. Tantrums were thrown – on both ends, he might add. Nate could still carry a mood with the best of them. She'd called him unprofessional, and a terrible worker.

Yet here she was, fresh out of Columbia J School and sitting on his desk, much like she would in the long-ago evenings as a surprise. Except she was wearing significantly more clothes this time around.

Nate looked up at her from the paper in his hands, impressed.

'Journalism and business? Not what I expected.'

'Well I'm just full of surprises.'

Sage was more relaxed now, legs uncrossed and slightly open. Nate tried hard to keep his eyes on her face, but she was making it very difficult. One hand slid down her neck, the other rested on her thigh. She clearly remembered just how much he liked a woman's neck, or more specifically the spot just between the neck and the collarbone. He swallowed. He was a professional, _dammit_, and she was being everything but. He moved around the desk and she jumped down to follow him. He sat in his chair.

'What's wrong?' she asked innocently, leaning over his computer.

'Sage, I don't know if you being my assistant is such a good idea.'

She pouted, and he wondered for a moment if she'd done any growing up in their four years apart. Really, she should have. He had potential investors sitting just a room away, waiting on the Editor in Chief himself to come through and explain to them why working with the Spectator was the best thing they'd ever do. He reminded himself to mention the jet again. Since expanding coast to coast, it just made things easier. Chuck had gifted it to him originally, but he'd paid his best friend back in full. Nate realized how hard he was concentrating on anything but Sage, who had come around to his side of the desk and now stood in front of him.

'I actually think it would do us both the world of good,' she explained, hands on the arms of his chair and leaning down.

She came eye level with him, and Nate stood up and out of her reach once again.

'Sage, this is ridiculous,' he said, laughing. 'I'd be your boss. We have a complicated enough past as it is – I don't think you working for me, and then working _it_ for me is a good idea. I'm sorry, the answer's no.'

She seemed disappointed for a moment, but soon perked up and gave him another smile.

'Well then, I guess this is okay.'

She closed the distance between them quickly, and Nate was so distracted by her rounding on him that he failed to notice Katie's voice in the hall once again.

'Go ahead, it's a free for all today.'

'Thanks!'

Sage kissed him full on the mouth, and he was taken back right away to when he was twenty two and they were spending late nights at the office, in every room, on every possible surface. He dropped her résumé on the floor just as the door opened and someone exclaimed:

'Oh, I'm sorry!'

Dazed by the sheer force of Sage's kiss, it took Nate a moment to focus on Jenny as she stood in the doorway, mouth agape and eyes wide with shock.

'I was just coming to say that I can't make lunch.'

She slammed the door just as quickly as she'd opened it and just in time too, as the investors had just started filing out of the conference room.

* * *

Sage is back! Didn't she say Little J used to be her idol once upon a time? I'm not sure it'll go down that way…

Please leave some feedback – it's much appreciated. Shout out to **Dr. Holland,** whose work I adore, and who leaves such lovely reviews! xoxo


	4. Party Planning

**A/N:** Hi everybody!

Sorry this chapter took a little longer than the rest!

This story has written itself so quickly, and there seems to be so much I need to get down. This is all good news, obviously, but I do admit that I'm surprising myself. Usually when I write the chapters don't flow so easily but with this story, everything's different. Might be the wonderful characters of the Upper East Side, and the wonderfulness of Nate Archibald and Jenny Humphrey (both together, and apart).

In this chapter, one of Jenny's boys makes his return to the Upper East Side in preparation for her birthday party, which Blair and Serena are planning right down to the last detail. What else could we expect, really? Her birthday is coming up soon, and boy it's going to be an interesting night! Nate also attempts to make up for the Sage incident by dropping by Dan and Serena's to see Jenny, and Chuck makes an interesting discovery when looking through a property contract.

Onward!

* * *

**Party Planning**

As Nate rode the elevator up to Dan and Serena's apartment, he mulled over the previous week's events. It all began, he would later realize, the day Jenny Humphrey returned to the Upper East Side full time. Blair had, for all intents and purposes, decided to throw and impromptu party, and Jenny and Nate appeared to have been the guests of honour. Nate had recently been informed by his best friend, Blair's husband, that Blair had a plan. And a Waldorf with a plan was like nothing else. Having pressed Chuck further, Nate soon discovered that this 'plan' was in fact to get Nate and Jenny to be one another's date for Dan and Serena's wedding. Apparently there was unresolved tension.

The two weren't engaged yet, but Dan was planning to ask and honestly, everyone already knew the answer.

In the days following the party, Nate had been cornered by his ex-girlfriend, Sage. When he turned her down for the position of his assistant, she turned the tables and kissed him, just in time for Jenny to burst into the room, and for countless potential investors to start filing into the Spectator's offices. Thankfully, they hadn't seen anything but Mr. Archibald politely declining an applicant, and an inexplicably frazzled young designer as she rushed from the building.

So Nate found himself heading to see Jenny to, if nothing else, apologize for the Sage incident. Although he wasn't sure an apology was needed, he certainly felt like he owed Jenny one. He didn't want her, of all people, to think he was still the same guy, going from girl to girl and never stopping long enough to actually be happy.

Jenny was staying with Dan and Serena. She was, as she put it that past Tuesday morning (it was now Wednesday), fed up of Blair's meddling and jibing about Carter Baizen. God, even the guy's name made Nate's skin crawl in disgust. He wanted to believe Jenny, but she'd had her fair share of crazy exes. Between Asher and Damien and, well, _himself_, her track record wasn't great.

The elevator binged and he stepped out into the hall. Serena and Dan's apartment was not the penthouse. Rather, it was a quaint – by UES standards, that is – little place nestled on the seventh floor, and they only shared said floor with one other apartment. Nate went to their door and knocked, expecting Dan or Serena first. Instead, it was Jenny who greeted him. She was out of breath, messy haired and red in the face. Safety pins and a pencil between her teeth, her hands were almost full with fabric and zips and buttons and god only knew what else.

Nate closed the door behind him and smiled. He followed her through to the guest room. There was fabric strewn everywhere, in pastels and golds, ribbons and cloths. Nate wasn't sure if there was even a carpet underneath it all anymore. Aghast at the state of the place, and wondering if Dan had seen it yet, Nate put his hands in his pockets and looked around some more. By then, Jenny had emptied her mouth of all non-essentials and was sitting at the dressing table; her sewing machine had taken pride of place, but she was sitting facing him instead of it.

'What's up, Nate?' she asked, and he wasn't sure but he thought she was quite short with him. It was probably the stress of having to answer to Blair Waldorf. He'd been there.

'Just wanted to check in,' he began, but stopped when she scooped up her cell and checked the screen. She put it right back down. 'How are you?'

'I'm good. I'm actually really busy –'

'Is this a bad time?'

They spoke in unison, and as they did Jenny's phone beeped. She swept it up twice as fast as before, but Nate didn't miss the disappointment on her face when she looked at the screen, and then put it down once again.

'You expecting someone?' he prodded. He had a good idea who, but chose not to dwell on it.

'No,' she replied, but again her gaze trailed down to her cell.

Nate was suddenly agitated. 'I just wanted to apologize for the other day – for what you walked in on, but you've clearly got other stuff going on so I can go.'

'You mean you and your assistant?'

'She's not my assistant,' he said, folding his arms.

'Definitely looked like she was assisting you with something –'

'Jenny,' he said pointedly. 'That was Sage Spence. My ex-girlfriend.'

'Oh, the seventeen year-old!' Jenny crossed her own arms and stood up. 'You were, what, twenty two when you dated her?'

'Why does that matter?' Nate asked, frowning.

Jenny didn't speak, only shook her head, and it dawned quickly on Nate that she was referring to them and, more specifically, herself. One of the biggest issues that came between them – after Vanessa's lies, but they were something else – was the age difference. It wasn't that big, granted, but Nate was already heading off to college and moving on by the time she turned sixteen. It wouldn't matter now, Nate knew, because she was turning twenty four on the weekend.

He looked her over. She was still long legs and skinny arms, but she'd grown into them and into a genuine beauty. Nate's didn't have a big preference, but on Jenny less was always more. She was naturally striking, and while he liked the platinum blonde, he didn't miss the black eyes and wine lips. Although he was partial to a nice colour lipstick. More accurately a lovely pair of lips, and Jenny definitely had those.

'Nate?'

'What?'

'You were staring.'

'Oh,' he caught himself and looked at the floor. 'Sorry. I'm tired.' _Liar_, he told himself. He was about to speak when she checked her phone again, and his agitation came flooding back. 'Why are you waiting on him?'

'Excuse me?'

'Baizen. I already told you, he's not worth it.'

'Why does it matter?' Jenny asked, matching his attitude and then some. 'It's not your business.'

'He's not worth it, Jenny.' Nate repeated, ignoring her when she rolled her eyes. For whatever reason, she'd stopped denying it. And that made him even angrier. 'He's not good enough for you!'

'And who is?' Jenny chastised. 'I can make my own decisions.'

'Your history with men begs to differ.'

Jenny half-laughed, half-glowered at him. 'You want to talk about dating history? We'll have to reschedule. Not sure your list of exes could fit in this apartment.'

It was Nate's turn to glower.

'This isn't about me.'

'I'm sorry, are you offended?' Jenny snarked.

Nate bit back a retort quickly. He observed her. Cheeks still rosy from her work, chest rising and falling rapidly in annoyance. He sighed loudly and threw up his hands.

'Jenny, I didn't come here to get in a fight.'

'Then why did you come?'

'I wanted to apologize for the other day.'

She rolled her eyes. 'Nate, I really don't care if you're banging your assistant. Or not your assistant, or whoever she is. It doesn't matter to me.'

Nate nodded, deeply unhappy at the turn of events. He was hoping for more a chuckle at the past and maybe something to eat. 'Well alright then.'

'I should get back to work,' she said, and even she sounded disappointed at the way things had gone. 'See you later.'

'Yeah, sure.'

He wasn't sure why he was lingering. She was just looking at him now, waiting on him to leave but he couldn't seem to get his feet to move ._Must be all that tension Blair is so convinced of_, he thought bitterly. Eventually, Jenny turned to her work and Nate knew he'd overstayed his welcome. He turned for the door and passed Dan, who was home from a meeting with his publicist.

'Just propose and get the damn wedding over with, would you?' Nate said in passing.

Dan looked up from his mail, puzzled. 'Good to see you too, man!' he called, but Nate was already gone.

* * *

'We're home!'

Jenny had never been happier to hear Serena's sing-song voice coming through the halls. She leapt up from her seat, threw down her fabric, narrowly avoided stabbing her feet with pins and rushed through to greet her soon-to-be sister in law, and then her best friend.

'Eric!' Jenny squealed, launching herself at him. She hadn't seen him in far too long. Eric was knocked into the wall by the force of Jenny's hug, but he didn't seem to mind as he wrapped his arms around her and held her tight.

'Six months is too long,' he said as they broke apart. 'You should get out to LA more often.'

'As much as I love bumping into faked up plastics and being whipped in the eye by hair extensions every time I turn around, I think I'll pass. You should move home,' Jenny said, ignoring the eye roll.

'LA isn't so bad,' Eric said.

They went through to the living room. Jenny and Eric got comfy and ready to catch up as Serena busied herself with making waffles. She'd become quite the force to be reckoned with since she and Dan had moved in together two years earlier, and her handy work in the kitchen was second to almost none. Serena was readying herself for motherhood, even if she didn't know it herself yet. All of her friends, Jenny included, could see her rushing around the kitchen as she prepared breakfasts for her doting husband and children. It would be sooner than she thought. Jenny observed Serena for a moment, then smiled and went back to Eric.

'Catch me up,' he said. 'What have I missed?'

It was half an hour later when Dan emerged from an afternoon writing session in his office. He yawned and stretched and then realized Eric had arrived and hugged his brother in law. When they parted, Dan looked down at Jenny. She was lying on her back on the couch, and Eric was sitting on the coffee table. It appeared to be a counselling session, although Eric probably wasn't charging her by the hour like he did all his other patients.

'What's uh… what's going on here?' Dan asked, looking between his sister, girlfriend and future brother in law. Serena was sitting in the armchair behind Eric, looking no more informed than Dan.

'Jenny's feeling some regret over a conversation she had with Nate earlier today,' Eric said, in his best psychologist's voice.

'We've been trying to work through it,' Serena added with a cheeky smile.

'So that's why Nate left here so pissed this morning,' Dan said, and Jenny groaned. 'What happened, Jen?'

'He's just so judgemental!'

'You're just learning this now?' Serena asked gently. 'Nate's always been that way. He's a great friend and he's a wonderful person. But if he doesn't like something, it's really hard to get him to see it clearly.'

'The way he kept going on about Carter –' She stopped herself and looked at Eric. So far she'd only told him about the Sage incident. _Damn it_, she thought.

'Carter?' Eric inquired, raising his eyebrows. 'As in Carter Baizen?'

'You didn't know about that whole…' Dan didn't try hard to hide his displeasure, 'thing?'

'I only knew about Nate and Sage. Jenny neglected to tell me the rest.'

'Because you can be just as judgy as Nate,' said Jenny, propping up on her elbows and poking her tongue out.

'This coming from Little J, former queen of Constance?'

'Don't you mean disgraced queen of Constance?' Jenny said, grabbing the nearest cushion and attempting to smother herself underneath it. Dan pulled it away and then forced her to sit up.

'Jen, what's really going on here?'

Jenny put her head in her hands. The truth was, Nate always, always seemed to press the right buttons. She could always rely on him to get her blood pumping. When she was a kid it was because she was crazy about him; the great Nate Archibald. As handsome as he was sweet, kind and an all-around good guy who didn't get lost in who his family was, or let anyone tell him what he could be. Jenny was consumed by him when she was younger, but as the years had worn on and she realized more and more how much he didn't want her back, she forced herself to get over him.

'I don't know. He just gets to me.'

'I wonder why,' Serena mused, sneaking a knowing glance Jenny's way. Jenny narrowed her eyes, but that only made Serena smirk.

'Can we get back to Carter?' Eric interjected suddenly. 'Because I'd like to know how that even happened in the first place.'

'London's a dangerous place,' Dan said, sitting on the arm of Serena's chair and pecking her on the lips.

'We just…' Jenny began slowly. 'We met over there, and we had fun. It doesn't even matter though because I haven't heard from him in a few days, so –'

'Is that unusual?' Dan asked.

Jenny didn't like where this was going. She'd been backed into a corner suddenly and now, here she was, about to confess her feelings about a guy she'd had no intention of developing feelings for in the first place. Not that she had feelings. She was just confused. She and Carter were friends, and they talked often, and that's what made his radio silence strange. She clasped her hands in her lap and soldiered on, because if she didn't talk about it to someone, it would just come out in another fight with someone else.

'A little. He called me the first morning I was here, and we usually text in the day. And so far… nothing.'

'Jenny,' Serena spoke up. 'If you like him, then you shouldn't let any of us – mainly Blair – tell you otherwise. If you say he's changed and you really believe that, then you shouldn't be afraid to be with him. If I had listened to Blair when she was telling me that I shouldn't be with Dan, we wouldn't be together now.'

Jenny sighed. 'Like I said, it doesn't even matter. We're just good friends.'

They all looked at her, but she chose to move on.

'Serena, are there any waffles left?'

* * *

'Everything is set.'

Blair Waldorf Bass stood in amongst chaos as her teams worked to prepare everything for Jenny's upcoming birthday party. With a clipboard and list of tasks on one hip, and a poorly Henry on the other, Blair tried to figure out if there was anything she'd missed. Of course there wasn't. Henry had his head resting on his mother's shoulder and was holding on to a lock of Blair's always-perfect hair. She turned and kissed the top of her son's head.

'What do you think, baby? Is Mommy the best?'

Henry didn't speak, but he did nod and Blair smiled in delight. Just then, the doors opened and Serena swept into the room, blinding the workers with her bright smile and nearly taking one's eye out with her long golden hair. She looked around the room and then gave Blair an approving nod. They'd decided to have the party in Chuck's newest building. Nestled on East 82nd Street, Penance was proving to a successful nightspot for society's elite. The children of senators and congressmen frequented the place, as did celebrities. The bouncers turned away anyone below the A list, naturally. Blair was certain Jenny would love it.

She'd decorated the room with two high-flying chandeliers. The lighting was low and romantic, and Blair was having white and lilac hydrangeas flown in from Japan. She remembered how much Jenny loved them in her younger years at Constance, and she was sure that taking Jenny back to a simpler time would only help Blair's plan to relight any fire Jenny still had burning for a certain Mr. Archibald. The theme of the party was simple; royalty. A girl only turns twenty four once.

'Jenny's going to love it, B.'

'Of course she will,' Blair said confidently, but she soon fell into a loving smile as Serena took Henry from her arms and wrapped him up in a great big hug. She soothed him and swayed and he soon fell asleep on her shoulder.

'He loves you,' Blair said and Serena grinned. 'Do you want something to eat?'

'No, thanks. I'm feeling a little queasy this morning.'

'I hope you don't have what my poor Henry does. How is it having Jenny living with you?'

Serena tried to remain tight-lipped, but Blair knew she'd get it out of her friend eventually. Jenny had opted to stay with her brother for the next couple of weeks, and while it meant there were no ample opportunities for Blair to prod her protégé for information about her romantic life, she did have Serena to employ on that front. Blair ran her hand over her son's forehead to check his temperature and then, satisfied, led Serena over to a leather booth so they could plan their next move. Serena wasn't aware of the full plan yet, and wouldn't be until Dan proposed. _If only Humphrey would hurry up!_

'Well… Jenny and Nate had a fight yesterday morning.'

'I knew something had happened,' Blair said, leaning across the table that divided them. 'He came over and went right to Chuck's expensive drinks cabinet.' He had two. One in the kitchen, the other in his office. The one in his office was reserved for truly dire situations or exceptionally joyous occasions. After disappearing into Chuck's office, Nate was eventually coaxed out when Blair told him dinner had been served.

'He had a face like thunder,' Blair said. Serena drew her lips into a thin line.

'From what Jenny told us it was because he brought up Carter. She's getting really sick of it, and she insists they're just friends.'

'Oh Little J,' Blair said in a sing-song voice. 'If it were really true she wouldn't be getting so agitated. No, something absolutely happened between her and Baizen, and we need to sever the tether before it's too late.'

'You make it sound so violent.'

'No violence necessary. A true queen knows how to play to her strengths.'

'And what are your strengths? I mean, besides the obvious?' Serena was smirking.

'Oh mon ami. The biggest thing we have working on our side is that I want to offer Jenny a permanent position here in Manhattan.'

'Just to keep her away from Carter?'

Blair looked appalled for a moment, before softening into a look of mild acceptance. 'I most certainly am not. Jenny Humphrey, though years ago I would have been loath to admit it, is very talented. She's smart, she understands this business and most importantly, she knows how this world works. And why wouldn't she? She learned from the best.' Blair said, looking pleased with herself.

'I am not giving Jenny this promotion just to keep her from Carter Baizen. That's just a pleasant, added bonus.'

Serena was rolling her eyes but, deep down, Blair knew she agreed. All their lives they'd heard stories of Carter Baizen. He was charming but certainly no prince, and he gambled away much of his inherited fortune by the time he was twenty one. But Blair had done her research upon learning he and Jenny were… _corresponding_. She'd discovered that Carter was making a vast fortune, atop the family money he came into when he turned twenty five, in the restaurant business.

'Well, either way, I think Jenny deserves the vice-president's position. She's more than earned it and maybe now that she's moving back to Manhattan full time, Eric will come too.'

Blair knew Serena desperately missed having her younger brother around. He was in town for the party but would be flying back to LA Monday evening. Blair reached over and touched her best friend's arm.

'He'll be back soon, I'm sure. The allure of our world is too strong to resist. Just look at Jenny – she could have stayed full time in Paris if she wanted. I even offered her a position over there but she turned it down. She always came back,' Blair said, then pulled a face. 'Even though London was calling.'

'So you'll offer her the promotion at her party?'

'And she'll be a fool to say no. It's a wonderful opportunity and it'll bring her home for good.'

'And what about Nate?' Serena said, surprising Blair. Blair took it in her stride.

'I just feel it would be a crime not to give them their fair shot,' she said. She couldn't say why, obviously. Blair had been on hand to help Dan choose the perfect ring. She suspected he was going to propose on the weekend. She hoped it wouldn't be on Saturday; she didn't want it to take away from Jenny's celebration, and all the praise she herself would inevitably get for the party.

Serena smiled. 'Saturday's going to be a big day for Jenny.'

And how right she was.

* * *

Chuck Bass was a busy man. He was a real estate mogul, a three time recipient of the Business Man of the Year Award, a self-employed billionaire and a chairman of several boards and committees. He was a brother and a best friend, but most importantly he was a husband and a father, and as he sat in his office, in his pyjamas and robe, rocking his four year-old son in his arms, he'd truly, never felt happier.

Henry had been sick all day. After arriving home with Blair, he'd thrown up on several pieces of furniture and on the hem of Blair's dress. Rather than scold him, however, Blair simply cuddled him before passing him to his father so she could change, clean up and then come and take care of her baby. After she'd fallen asleep in bed, with Henry wrapped in her arms, Chuck had gotten up and begun heading downstairs to do some late night reading.

Henry had called out and said he wanted his Daddy and so Chuck had taken his son with him to his office where they now sat. With Henry hugged close to his chest, sucking on his thumb, Chuck went about his reading. He was looking over paper for an expansion of property in the West Village, where he'd been eyeing an old building that, if fixed up properly, could become a wonderful night spot.

It just so happened – he later discovered – that another entrepreneur, who mainly dealt in things overseas, was also interested in the building. Chuck had, of course, stuck his PI on the tail of this businessman from London, and finally Chuck had the documents on his desk. When he read the name of the man, he had to double check.

'What?' he said to himself, careful not to wake his boy. He checked Henry was still fast asleep, and then went back to the papers.

So Carter Baizen was planning to open a restaurant in Manhattan, and apparently he already had a name in mind. Chuck was somewhat tempted to let him win the auction, just to amuse himself with thoughts of Carter trying to play with the big boys. Despite being the oldest, Carter had always been one of the most immature pieces of trash Chuck had had the misfortune of knowing. And by the look of the name of the restaurant, it seemed Chuck's darling wife was on to something when she lectured Jenny Humphrey about who she was rolling around the sheets with.

Jenny, of course, had denied it all.

But given that Carter planned to open a restaurant called J, Chuck suspected Jenny wasn't quite being honest.

* * *

**A/N:** Ugh, I'm sorry but Daddy!Chuck is literally one of my favourite things! Hope you liked the update - things are going to start heating up soon!  
Please leave some feedback - it's much appreciated! x


	5. Victoria Secret

**A/N:** This chapter gave me hell. I did not enjoy writing it at all. It just didn't flow like the others have, but I really hope that doesn't reflect too much in the writing. I know it took a while and I'm sorry about that! I think once Jenny's birthday has been and gone, the story will really start to pick up speed.

The main thing I wanted to establish in this chapter was Carter, and I'm actually really happy with that part.

Onward!

* * *

**Victoria Secret**

* * *

'Jen!'

The pounding knock on the bedroom door woke Jenny from a deep, vodka induced sleep. She turned her head to the side and found Eric lying next to her on the bed, still in his shirt and trousers. He groaned loudly and rolled onto his stomach, then buried his head under one of the six pillows. What was it with rich people and pillows? Jenny pushed herself up onto her elbows and surveyed the mess that was her room. More accurately, Dan and Serena's guest room. And she and Eric looked to have destroyed it. There were scattered bottles of alcohol, empty cups and lots of chick flicks strewn across the floor.

'Oh, no…' Jenny muttered, rubbing her eyes. Surprisingly, she didn't have a headache. But she felt wretched in her stomach.

It had been a night spent reminiscing and confessing, though Jenny chose to ignore just exactly what she'd confessed. She suspected Eric would tease her about Carter endlessly later on.

'Come on, Jenny. Let's get breakfast,' Dan called to her through the door.

She replied with a groan much like Eric's, but within fifteen minutes she'd managed to scrape herself together to head out for a morning bagel. Her hair was up in a top bun, she'd pulled on some light wash jeans, tan ankle boots and a cream blouse. Finally, she added a leather jacket. The one downfall of being a designer was that the press always wanted pictures. No matter if she was just running to the store, or heading downtown to get a manicure, or just to the atelier, she always had to look her best.

'You reflect on Waldorf, and if you look bad, Waldorf looks bad,' she muttered to herself, Blair's words emanating from her memory.

Grabbing her bag and slipping her sunglasses on, she met Dan in the hallway after brushing her teeth.

'You look like hell,' he said, feigning sympathy. Jenny hit him on the arm and they headed out.

Half an hour later, after they'd decided to get coffee and a bagel to go, they found themselves wandering around Central Park. It had been a while since Jenny had taken a breath and looked around, and only then did she realize how much she missed just that; wandering. For years she'd had goals. She'd achieved so much in such little time, and now that she was home she wondered if maybe she should slow down and drink it all in. Of course there was still the spring line to consider for next year, but she did miss idle summer days spent with her family. Speaking of…

'Have you spoken to Mom?'

'No,' Dan said sternly, taking a swig of his coffee to avoid a more in depth answer.

Jenny tried not to roll her eyes but it was no use. Ever since The Incident, Dan had avoided any and all contact with their mother. Even his Dad's reasoning hadn't worked. Dan had always been stubborn, but it was starting to get ridiculous and even though he was justified in his annoyance, Jenny wasn't sure how much more of this rift she could take.

'She's sorry you know. She didn't mean it –'

'Yes she did,' Dan said, stopping in his tracks and turning to her with a half-laugh. 'She did mean it, and it was hurtful. To Serena and to me. If she is sorry, she has a funny way of showing it with her lack of phone calls and her lack of texts and emails and everything.'

Jenny was resigned. 'Fair enough. She has tried calling, though. You've just never picked up.'

'Yeah, the first few times because I didn't want to say something I'd regret. Then she just stopped, like it didn't matter anymore.'

Jenny led him to a nearby bench. 'Has anyone ever told you you're a pain in the ass, Humphrey?'

'Has anyone ever told you you're a terrible liar, Humphrey?'

Jenny scowled at him and drank the rest of her coffee.

'Kidding, you're actually scarily good at it.'

'Aren't we all?' Jenny challenged, hooking an eyebrow.

'Fair enough. What I mean is… there's something there, isn't there? With you and Carter?'

'Not this again,' Jenny groaned. 'I already spilled enough to Eric last night, even if I can't remember just how much.'

'Oh I know you did.' Dan was grinning. 'You're pretty loud when you're drunk. Plus Serena was throwing up all night and she had stomach cramps, so I didn't get much sleep anyway.'

'Is she okay this morning?'

'I think so. She's tired but she's gone to take care of Henry for a few hours. I think she caught whatever he had a few days ago. And don't change the subject – I know you like Carter, and like wasn't the only L word you threw around last night.'

'Oh, God!' Jenny put her head in her hands, praying for anything to help her forget. Luckily, Dan had just the thing.

'Alright, never mind Carter for now. What happened with you and Nate?'

'Oh God, oh God,' she repeated, looking at him through her fingers. 'This is just the worst week.'

'He was pretty upset when he left. Told me to get the damn proposal over with already.'

'Honestly Dan I think that would be best for everyone.'

He laughed briefly, but it faded and there was a glint in his eye as he looked at her.

'I don't get you two.'

'What's to get?' Jenny asked, frowning.

'Never mind. It's just… he cares about you, you know? He always asked about you when you were away, always wanted to make sure you were okay, and he always took care of you when you needed him. I don't understand why the two of you can't seem to just… figure it out. You should talk to him.'

Jenny rolled her eyes. 'I think I'd rather talk about Carter.'

Dan threw an arm around her shoulders as they stood up and began the walk back to his apartment.

'Seriously, I think you two should talk.'

* * *

'Serena, hey.' Nate kissed her cheek as she came through his office door with a sleeping Henry on her hip. He took her bag and pulled out the chair opposite his desk for her to sit. Henry woke up quite suddenly and, after Serena had set him down, he took a running jump at his godfather and giggled as Nate swung him up into his arms.

'Hey, buddy! You feeling better?'

'Yes!'

'Yes…?' Serena chided him, raising her eyebrows expectantly.

Henry took his cue with a smile. 'Yes, thank you!'

'Good,' Nate said, ruffling his hair. He set him down and led him over to a trunk he had in the corner of his office. Henry immediately threw the lid open so that it banged against the wall, but Nate only smiled wider as Henry pulled out toys upon toys out. With Henry occupied, Nate strolled back to his desk and sat down opposite Serena.

'How long have you had those toys here?'

'About three years,' Nate said, chuckling. 'I love that kid. So, what can I do for you?'

'A friend can't just visit a friend for lunch?'

'Serena, it's ten thirty.'

'Breakfast, then?'

'Of course a friend can,' said Nate, knitting his fingers together in his lap. 'But that's just it. We're friends. I know something's wrong, so tell me.'

Serena's gaze travelled to Henry, and her heart skipped at the sight of him with his dumper trucks and his little colourful abacus. He looked so happy, so fulfilled, and she knew that he was so loved. It made her ache inside, and suddenly her eyes were welling.

'Do you want kids, Nate?'

He looked surprised by the question and took a moment to compose himself before answering with a smile.

'Of course. Whenever I'm with Henry I think about the day that it's my own son, or daughter, and it excites me. Why do you ask?'

Serena wiped at her eyes and tactfully covered her sadness with her million dollar smile. But Nate could always see right through her and he practically leapt over the table to sit beside her and take her hands in his.

'What is it?' he asked. 'Are you okay?'

'Nate, I think I'm pregnant,' she admitted, and then collapsed into tears in his arms.

'Woah, woah,' he said. 'It's okay. Isn't this a good thing?'

'We're not married, and normally that's not a big deal but for us, in this world, it does, a-and we're not… Dan's so stressed with his new book, and there's so much going on with me and the committees and it's just not the right time, and we're still not speaking with his mother and I just… I can't… I don't know what to do.'

'Serena, don't cry!' Henry suddenly shouted, careering towards her and throwing himself into her lap. He hugged her fiercely around the middle. Nate touched Henry's cheek and then Serena's, and she was struck suddenly into calmness.

She'd be lying if she said that, in her younger years when part of her heart belonged to Nate, she hadn't imagined the two of them making a life together. Even though it was supposed to be Blair and Nate, Serena had always been a defining factor in all of Nate's relationships, and she knew that. She felt bad that most of his girlfriends scurried away at the smallest mention of Serena Van der Woodsen. He'd loved her for years, and she'd felt guilty for longer.

Sitting there with him and Henry in her lap, they looked like a little family. Serena smiled. Nate was her family, and he always would be. But no one could ever come close to Dan's place in her life. He was everything. Nate wiped away a stray tear and left his hand on her cheek.

'Dan's the luckiest guy in the world, and he loves you so much. You're going to be amazing parents.'

'Thank you, Nate.' She leaned into his touch.

Someone cleared their throat in the doorway, and they both turned to find Jenny watching them, arms crossed and eyebrows raised higher than the Empire State Building.

* * *

Carter had never been good at picking gifts. During his short-lived romance with Serena Van der Woodsen, he'd wanted to spoil her but, at the time, money had been something of an issue. Now, with Jenny, he was financially secure and that was just him being modest. He was rich, and he liked the gifts he gave to reflect that. But he was terrible at choosing things, even for someone he knew as well as Jenny. He thought about calling on Erin to help, but he knew that Jenny would suss him out right away and at the very least, he wanted to surprise her by doing something of his own accord.

He wasn't too sure about Jenny Humphrey. He was sure he liked her, of course. God, she was brilliant. Street smart and intellectual and beautiful and able to play a good game or two, but the sudden rush of feeling when she'd told him she might not be coming back to London had him panicked. They weren't supposed to be anything. She was the best sex he'd ever had, and he'd had his fair share. Something was different with Jenny, and he couldn't put his finger on what exactly it was.

So it remained that he liked her, and that in itself was a problem. He liked her enough to be debating gifts for a person who was half a world away, and he had a sinking feeling that he was alone in his feelings. But then she had seemed so… disheartened on the phone, and that was his fault really. He'd been unenthusiastic when talking about her birthday, but it was just a facade. A well-honed method of coping. Growing up on the Upper East Side made actors of them all, and Carter could hide his feelings with the best of them. But something about Jenny made him want to stop hiding.

And Jesus Christ, that was scary.

His desk phone buzzed and Erin's voice chimed into his thoughts.

'The real estate agent from Manhattan is on the line. Are you in the office?'

Ah, the pinnacle of his last few months' work. His new restaurant, which he'd been planning for a while now but had only recently named, was set to be a popular night spot; if he could only wrangle the property he really wanted. There was interest from another party, and Carter was sure it was going to go to auction. He had plenty of funds to back himself up, and he truly loved what he did, but it was a commitment.

Not just to his career, but to Jenny. J was for her, and as much as he ignored the fact, it was slowly dawning on him that this was a _serious_ thing. This playful, friends with benefits, sex at all hours and no commitment had rapidly becomes movies on pay per view in their pyjamas, spending the nights just sleeping, wrapped up in each other, and talking every day. Carter had fallen hard, but he couldn't pinpoint when or where.

'Mr Baizen?' Erin prompted.

He cleared his throat and swung his feet down off the desk.

'Tell Miss Thorpe I'll call her back. I have some errands to run.'

It came to him as he walked the streets of Soho, then caught the tube to the Embankment and from there walked to Chelsea. He loved this city more than New York. There was something in the air; a closeness of people despite the sheer size of the place. He loved to walk around in the free air, in the place he'd found himself after years of running away and pissing away his family name and wealth. He was man now, with things he treasured and wanted to last.

His feet wandered with his thoughts and, before long, he was outside The Corner Place, and staring at him through the window was Jenny's very favourite cake. Victoria Sponge. Smiling to himself, he pulled out his cell and dialled his assistant's number.

'Erin,' he said, beaming, when she answered promptly. 'Scramble the jet and my pilot for this Saturday.'

Erin sighed and then, under her breath, muttered 'finally'. Carter smiled wider and put the phone down, then said to himself:

'There's someone I need to get to.'

* * *

_I know this is much shorter than the others, sorry! Buuut it looks like things are about to get veeery interesting on the Upper East Side. _  
_Please review! It makes my day x_


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